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Method for preparing N-(carbobenzoxy) succinimide

A technology of hydroxysuccinimide and succinimide is applied in the field of preparation of N-(benzyloxycarbonyl)succinimide, which can solve the problems of poor purity and low product yield, and achieve good purity and reaction yield. High efficiency and simple operation

Inactive Publication Date: 2014-05-14
GENCHEM & GENPHARM CHANGZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved in the present invention is: to overcome the technical deficiencies of low product yield and poor purity in the prior art, and to provide a preparation method of N-(benzyloxycarbonyl) succinimide with high product yield and good purity

Method used

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  • Method for preparing N-(carbobenzoxy) succinimide

Examples

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Comparison scheme
Effect test

Embodiment 1

[0022] A preparation method of N-(benzyloxycarbonyl) succinimide, the preparation method comprising the following steps:

[0023] (1) 57.5kg N-hydroxysuccinimide, 82.8kg K 2 CO 3 , 552kg of deionized water and 287.5kg of butyl acetate were dropped into a 1000-liter reactor.

[0024] (2) Cool with jacketed ice-salt water to an internal temperature of 9-10°C, add 85kg of benzyl chloroformate dropwise while stirring, and complete the addition within 2-3 hours. Continue to keep the internal temperature at 5-15°C for 1 hour after adding After the addition was complete, the reaction was continued for 1 h.

[0025] (3) Stop stirring after the reaction is over. After standing still for 1 hour, the lower layer of brine is released, and the upper layer of ethyl acetate remains in the reaction kettle. After stirring, add 287.5 kg of petroleum ether next time, and stir for another 1 hour at room temperature. A large amount of white solids are precipitated. .

[0026] (4) The wet produ...

Embodiment 2

[0028] A preparation method of N-(benzyloxycarbonyl) succinimide, the preparation method comprising the following steps:

[0029] (1) Mix 57.5kg N-hydroxysuccinimide, 34.5kg K 2 CO 3 , 690kg of deionized water and 57.5kg of butyl acetate were put into a 2000-liter reactor.

[0030] (2) Cool with jacket ice brine to an internal temperature of 0-9°C, add 68.2kg of benzyl chloroformate dropwise while stirring, and keep the internal temperature at 0-15°C after adding 68.2kg of benzyl chloroformate within 0.5 hours 5h, continue the reaction for 1h after the dropwise addition is completed.

[0031] (3) Stop stirring after the reaction is over. After standing for 1 hour, the lower layer of brine is released, and the upper layer of ethyl acetate remains in the reaction kettle. After stirring, 575 kg of petroleum ether is added next time, and stirred for another 1 hour at room temperature, and a large amount of white solids are precipitated.

[0032] (4) The wet product was obtained...

Embodiment 3

[0034] A preparation method of N-(benzyloxycarbonyl) succinimide, the preparation method comprising the following steps:

[0035] (1) Mix 57.5kg N-hydroxysuccinimide, 138kg K 2 CO 3 , 690kg of deionized water and 862.5kg of butyl acetate were put into a 3000-liter reactor.

[0036] (2) Control the temperature at 10-60°C, add 102.3kg of benzyl chloroformate dropwise while stirring, and continue to keep the internal temperature at 50-60°C for 0.5h after adding 102.3kg of benzyl chloroformate for 5 hours. Continue to react for 1h.

[0037] (3) Stop stirring after the reaction is over. After standing still for 1 hour, the lower layer of brine is released, and the upper layer of ethyl acetate remains in the reaction kettle. After stirring, add 1752 kg of petroleum ether next time, and stir for another 1 hour at room temperature, and a large amount of white solids precipitate out.

[0038] (4) The wet product was obtained by filtration, taken out after pressing, and dried in an o...

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Abstract

The invention relates to the field of refined chemical, and in particular relates to a method for preparing N-(carbobenzoxy) succinimide. The method comprises the following steps: (1) feeding N-hydroxy succinimide, an alkali water solution and an organic solvent which is not mutually dissolved with water into a reaction device, (2) dropwise adding benzyl chloroformate at 0-60 DEG C and then further reacting for 1 hour, (3) stopping stirring when the reaction stops, standing for 1-2 hours so that the water phase at the upper layer and the water phase at the lower layer are separated; then discharging the water phase at the lower layer; adding petroleum ether after the organic phase is separated out; stirring for 1 / 2-1 hour at the room temperature to separate out a solid product, and (4) filtering to obtain a wet product, and drying to obtain the product, namely the N-(carbobenzoxy) succinimide. The technical scheme of the invention has the beneficial effects that the N-(carbobenzoxy) succinimide is produced by using a one-pot method, the operation is simple, the reaction yield is high, the product, namelyN-(carbobenzoxy) succinimide has high purity and is applicable to industrial production.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a preparation method of N-(benzyloxycarbonyl)succinimide. Background technique [0002] N-(Benzyloxycarbonyl)succinimide, CAS (13139-17-8), is a commonly used amino acid protective agent in peptide synthesis, and is widely used in the synthesis of peptide drugs. Its molecular weight is 249.23, its melting point is 80-82°C, and its structural formula is as follows: [0003] [0004] There are generally two methods for the synthesis of N-(benzyloxycarbonyl)succinimide using benzyl chloroformate and N-hydroxysuccinimide. One is to use an organic solvent system, such as the method published by Anteunis M.J.O in French magazine Bull.Soc.Chim96 (10), P775 (1987) in 1987, using triethylamine organic base, reacting in tetrahydrofuran solvent, and then passing through The crude product was purified after removal of triethylamine hydrochloride to obtain N-(benzyloxycarbonyl)succinimide w...

Claims

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Application Information

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IPC IPC(8): C07D207/46
CPCC07D207/46
Inventor 王玉琴詹玉进
Owner GENCHEM & GENPHARM CHANGZHOU CO LTD
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